3-azido-N-tosylpropan-1-amine | 1160749-95-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-azido-N-tosylpropan-1-amine
• 英文别名: N-(3-azidopropyl)-4-methylbenzenesulfonamide
• CAS: 1160749-95-0
• 化学式: C₁₀H₁₄N₄O₂S
• mdl: MFCD13452426
• 分子量: 254.313
• InChiKey: LSAOHMDZIOFYBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-azido-N-tosylpropan-1-amine 、 2-萘甲醛 在 三氟甲磺酸 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以91%的产率得到
  参考文献：
  名称：

  芳香醛与叠氮基胺的施密特反应形成的无金属N-芳基化反应

  摘要：

  在酸的存在下，通过施密特方法实现了芳香醛与3-叠氮基-N-甲苯磺酰基丙烷-1-胺的无金属形式的N-芳基化反应。发现TfOH是良好的促进剂，并且观察到排他的1，2-芳基迁移。此外，以优异的产率实现了脂族醛向N，N-二取代甲酰胺的转化。

  DOI：

  10.1021/ol400213f
• 作为产物：
  描述：

  N-(3-chloropropyl)-4-methylbenzenesulfonamide 在 sodium azide 、 四丁基碘化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以4.58 g的产率得到3-azido-N-tosylpropan-1-amine
  参考文献：
  名称：

  芳香醛与叠氮基胺的施密特反应形成的无金属N-芳基化反应

  摘要：

  在酸的存在下，通过施密特方法实现了芳香醛与3-叠氮基-N-甲苯磺酰基丙烷-1-胺的无金属形式的N-芳基化反应。发现TfOH是良好的促进剂，并且观察到排他的1，2-芳基迁移。此外，以优异的产率实现了脂族醛向N，N-二取代甲酰胺的转化。

  DOI：

  10.1021/ol400213f

文献信息

• High-Throughput Discovery of <i>Mycobacterium tuberculosis</i> Protein Tyrosine Phosphatase B (MptpB) Inhibitors Using Click Chemistry
  作者：Lay Pheng Tan、Hao Wu、Peng-Yu Yang、Karunakaran A. Kalesh、Xiaohua Zhang、Mingyu Hu、Rajavel Srinivasan、Shao Q. Yao

  DOI：10.1021/ol9023419

  日期：2009.11.19

  A ∼3500-member library of bidentate inhibitors against protein tyrosine phosphatases (PTPs) was rapidly assembled using click chemistry. Subsequent high-throughput screening had led to the discovery of highly potent (Ki as low as 150 nM) and selective MptpB inhibitors, some of which represent the most potent MptpB inhibitors developed to date.

  使用点击化学快速组装了约3500个成员的针对蛋白质酪氨酸磷酸酶（PTP）的二齿抑制剂文库。随后的高通量筛选导致发现了高效的（K i低至150 nM）和选择性的MPTpB抑制剂，其中一些代表了迄今为止开发的最有效的MPTpB抑制剂。
• Rhodium-Catalyzed Intermolecular Reaction of Alkyl Azides with Diazo(aryl)acetates
  作者：Peiming Gu、Xiu-Ping Wu、Yan Su、Xue-Qiang Li、Ping Xue、Rui Li

  DOI：10.1055/s-0033-1340173

  日期：——

  An efficient intermolecular interception of alkyl azides by diazo(aryl)acetates was achieved in the presence of dirhodium tetraoctanoate. The initial products were unstable α-imino esters, and overaddition of carbenoids to the C–N double bonds was avoided. After acidic workup, the corresponding α-keto esters were obtained in good to excellent yields.

  在四辛酸二铑的存在下实现了重氮（芳基）乙酸酯对烷基叠氮化物的有效分子间拦截。初始产物是不稳定的 α-亚氨基酯，避免了类卡宾在 C-N 双键上的过度加成。酸处理后，相应的α-酮酯以良好到极好的收率获得。
• Fragment-based discovery of novel and selective mPGES-1 inhibitors Part 1: Identification of sulfonamido-1,2,3-triazole-4,5-dicarboxylic acid
  作者：Kijae Lee、Van Chung Pham、Min Ji Choi、Kyung Ju Kim、Kyung-Tae Lee、Seong-Gu Han、Yeon Gyu Yu、Jae Yeol Lee

  DOI：10.1016/j.bmcl.2012.11.019

  日期：2013.1

  Microsomal prostaglandin E synthase-1 (mPGES-1) is an inducible prostaglandin E synthase that catalyzes the conversion of prostaglandin PGH(2) to PGE(2) and represents a novel target for therapeutic treatment of inflammatory disorders. It is essential to identify mPGES-1 inhibitor with novel scaffold as new hit or lead compound for the purpose of the next-generation anti-inflammatory drugs. Herein we report the discovery of sulfonamido-1,2,3-triazole-4,5-dicarboxylic derivatives as a novel class of mPGES-1 inhibitors identified through fragment-based virtual screening and in vitro assays on the inhibitory activity of the actual compounds. 1-[2-(N-Phenylbenzenesulfonamido)ethyl]-1H-1,2,3-triazole-4,5-dicarboxylic acid (6f) inhibits human mPGES-1 (IC50 of 1.1 mu M) with high selectivity (ca. 1000-fold) over both COX-1 and COX-2 in a cell-free assay. In addition, the activity of compound 6f was again tested at 10 mu M concentration in presence of 0.1% Triton X-100 and found to be reduced to 1/4 of its original activity without this detergent. Compared to the complete loss of activity of nuisance inhibitor with the detergent, therefore, compound 6f would be regarded as a partial nuisance inhibitor of mPGES-1 with a novel scaffold for the optimal design of more potent mPGES-1 inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.